And He Knows It
by PwnedByPineapple
Summary: Dean is just too pretty for his own good sometimes. Luckily, Sam's always got his back. Also, Sam "learns" a thing or two. Includes teen!chester, hurt!Dean, protective!Sam, and brotherly fluff.


**Title:** And He Knows It  
**Author:** PwnedByPineapple  
**Summary:** _Dean is just too pretty for his own good sometimes. Luckily, Sam's always got his back. Also, Sam "learns" a thing or two. Includes teen!chester, hurt!Dean, protective!Sam, and brotherly fluff.  
_**Rating/Warning(s):** T; a little mention of some sensitive subject matter  
**Notes:** Birthday gift for Spnoth of deviantART, who loves Dean. Takes place fairly early on in the series, so no spoilers.

**Disclaimer: This fangirl owns nothing.**

* * *

_The site of the lesson was... fairly unusual, in Sam's estimation._

_"Um... Dean?" the younger Winchester said, gazing around at the school's courtyard in bafflement before returning his attention to his brother. "I thought you said you were going to give me a hunting lesson." He'd expected the woods behind the school, maybe, but not this, in plain view of all of the students._

_"I am," Dean replied, rather smugly. He seated himself on one of the empty benches at the edge of the courtyard and indicated for Sam to do the same. "Take a seat, little bro. Today, you get the most important lesson of all."_

_Sam had been honing his instincts as of late, and they told him that something strange was going on. But it was Dean, and so he acquiesced, gingerly seating himself beside his brother and wondering why they couldn't just wait until after school had finished. He was wasting lunch time for this._

_"What **are **we doing?" Sam wanted to know._

_Dean's smirk was matched only by the gleam in his eyes. "Today," he said by way of answering, as if relishing the words leaving his mouth, "I'm gonna teach you about girls."_

* * *

There were a great many beautiful women at the bar that night, but Sam Winchester had his eyes set on one.

She hadn't found herself a date for the evening... yet. Assuming Sam could pull this off, that would soon change. And he _had _to pull it off; there simply was no other option, because Sam was nothing if not stubborn, and by God he'd make Dean proud tonight. He had to have something good to tell his brother later, after all.

He approached slowly, purposefully, calling to mind moments when they'd been young and Dean had attempted to teach him the art of picking up women. Needless to say, those had been some of Sam's more interesting hunting lessons, and he wasn't too sure what he'd been supposed to come away with. But it would have to be enough. He wasn't lacking in certain charms, after all.

"Oh, I'm sorry!" he said to her, gentlemanly apology in his tone. With a few casual, subtle steps, he'd 'accidentally' bumped her shoulder, causing her drink to slosh a bit in its glass. It hadn't spilled, but he made a fuss anyway, apologizing again and showing more interest than he ever would have. She wasn't his type - all exposed skin and too-noticeable curves, clearly trying to attract attention. But it didn't matter what his type was. All that mattered was Dean.

"Not at all," the woman said, brushing a strand of blonde hair out of her appraising eyes as she gave Sam a thorough once-over. He hoped to God that she liked what she saw, and maybe someone was listening, because she didn't make to move away or seem disinterested. "My fault, of course. You're so big and tall, and I just didn't move out of the way fast enough!" To his ears, her voice was nauseatingly flirty and seductive, or maybe that was just because he speculated at her true nature. "I'll need to find some way to say sorry, you know." She gave him a little grin, her head cocked slightly to the side.

He made himself smile - natural, easy, don't let her know what you're thinking, Sam. "Oh, I can think of a few ways," he added. Insinuation, Dean had once said - these kinds of girls would love that stuff. "But whoever's fault it was, your drink definitely needs a refill. Let me buy one for you."

The woman's grin became a giggle. "Ooh, so chivalrous. I may faint." With a fluid motion, she handed him her glass, and her fingers lingered against his longer than necessary. "Knock yourself out, sir. My apology will come later."

_I'll bet it will,_ Sam thought darkly, but he didn't let this thought reach his eyes, and he turned to flag down the bartender.

* * *

_"Now, it all depends on the girl," Dean was saying, and his tone had become remarkably businesslike for someone who was lecturing his younger brother on picking up chicks. "Some of them will give in like that." He snapped his fingers for effect. "You stick with those. If a girl turns you down or ignores you, and she's not just playin' hard-to-get, then you know she's too good for you. So you move on. Got it?"_

_"I... think so," Sam said uncertainly; not because he didn't understand, but because he hadn't even been expecting this in the first place. He was barely through teenager-hood as it was! Girls had certainly become more interesting, yes, but he and his family were on the move far too often for him to pursue any kind of real relationship with one._

_But somehow, he didn't think what Dean was talking about had anything to do with 'real' relationships._

_His brother had moved on to something else, but Sam stopped him in mid-sentence, clearing his throat. "Sorry," the younger Winchester said, "but I don't really understand why you're telling me this."_

_Dean gave him an exasperated look. "It ain't that hard to figure out, Sammy. To get girls."_

_"Sam, and I know that. But we never stay in one place long enough, Dean. I'm never going to get a girlfriend if we keep that up."_

_Dean chuckled at this. "Not exactly what I'm talking about, lil' bro."_

_And the older Winchester's smirk became a frown at Sam's blank look. "Oh, come on," Dean said. "You know what I mean. Getting some."_

_"Some what?" Sam asked, with a shake of his head._

_He didn't understand the dawning look of horror that stole across Dean's face at this. Dean had the appearance of one struck dumb by a terrifying revelation, which didn't make any sense as far as Sam was concerned. "Oh, God," said Dean, almost a whisper. "Sam. Did... did Dad tell you about the birds and the bees yet?"_

_Sometimes, Sam's older brother was just hopeless. "The **what**?" Sam demanded. How on earth had they gone from girls to animals?_

_Dean was turning an interesting color. "Oh, God," he said again. "Oh man. Dammit, Dad. Really? He's already fourteen!" Even though their Dad was nowhere around. "And now... aw, shit." To Sam's somewhat alarmed relief, a small grin came back to Dean's face, though it didn't form the most pleasant of expressions. He looked hesitant now, almost embarrassed. "I guess I'll have to. Shit."_

_"Have to what?" Sam asked tiredly. He'd had enough of 'what' by now._

_After casting a furtive glance around to make sure that there was no one near them, Dean wrapped an arm around Sam's shoulders and leaned in close. "Okay, buddy," he muttered. "I'm going to tell you something crazy and awesome. But you can't ask me any complicated questions because **I don't know**, alright?"_

_Sam's curiosity was piqued despite himself. Was it some kind of secret that Dad and Dean had been keeping from him? And what did it have to do with Dean's lesson?_

_Sam nodded in assent, and so Dean began._

* * *

On Katrina's invitation, Sam entered her house first and had perhaps three seconds before she pounced on him.

In those three seconds, the sight that greeted his eyes caused a sickening surge in his stomach that was part relief, part horror, and part fear - though not for himself.

_Dean. _Dean was alive, though that was the extent of Sam's relief. The older Winchester, bloodied and pale, was on the floor and seemed to be in the process of crawling towards the phone on a desk, though he'd frozen in place with his eyes glazed in pain and shock.

Sam barely had time to register this before he heard the door slam, a lock click, and he couldn't even turn before inhumanly strong and manicured hands latched on to him and threw him to the ground. His head spun when the back of his skull made painful contact with the floor, and an enormous weight settled on him, not at all in keeping with Katrina's petite size. "How are you awake?" he heard her snarl at Dean, and then her face was in Sam's, black eyes gleaming with malice. "Oh, well. I'd hoped we could have a night together, big handsome thing like you, but it looks like it's time for you to take a nap."

_Her lips, don't let them touch you. _Gritting his teeth, Sam turned his head to side as far as he could and forced himself to stop resisting her hold on him. Instead, his muscles tensed and bunched as he reached into his jacket.

A moment later, Katrina screamed and leapt off of him, and Sam felt the Holy Water splash his stomach as well. Keeping the bottle clutched in a tight grip between himself and the demon, Sam climbed to his feet, backing up towards Dean as he did so. Dean had used the desk containing the phone to pull himself to his feet, but Sam could see that his legs were trembling, threatening to give out on him at any moment.

"You okay?" Sam asked - a stupid question in hindsight, but he had to know that nothing was life-threatening.

"Just... fucking... peachy," Dean muttered, and the snark reassured Sam. He grabbed Dean's arm, lending him support, and turned a glare on Katrina.

A succubus. He'd been right in his assumption that one was in town and had taken Dean as her prey, and he'd be damned if he let her get away with it. She was returning his glare with venom in her pitch black eyes. "You're a hunter?" she spat out, and Sam didn't answer. "Well, that's just my luck. Not all hunters are as good-looking as you." Katrina grinned. "Doesn't matter. You aren't leaving either, sweetheart."

A swift glance was all Sam had to exchange with his brother, a couple of unobtrusive movements, and Sam knew everything he needed. He carefully released Dean's arm, and Dean almost immediately buckled under his own weight, swearing as he did so. "Stay there," Sam told him, taking a few steps forward.

Katrina smirked at this. "You hunters, always trying to be heroes."

Sam responded by flinging more Holy Water in a wide arc, and though the demon ducked, she couldn't avoid all of it. While she screamed, clutching at her arm, Sam began speaking as fast as possible, the Latin words flying out of his mouth.

"Not so fast," Katrina snarled, and a coffee table came flying at Sam's head. He ducked and stumbled, sliding to his knees, but after only a gasp he grimly resumed the exorcism.

Katrina lunged for him, but Sam flung the last of the Holy Water in her direction, forcing her back. And then he was out of defense, still gasping out the Latin, until the succubus landed on top of him, forcing him to the ground and squeezing his throat. Her grin, never far from her face, grew wide and triumphant as he squirmed beneath her. "Aww, and you were so close."

And Sam, faintly hearing the muttered chanting over the pounding in his ears, returned the grin even as he struggled for breath. "Closer than you think," he gasped.

Realization flashed in Katrina's eyes, and she released Sam to spin around. Coughing, Sam curled upward just in time to see Dean pause at the end of the exorcism, flashing Katrina a smirk from where he was propped up against the desk.

"I'm a hunter too, bitch," he growled, and continued.

Katrina made a violent move towards him, but she was caught now. The exorcism held her rigid as it tried to expel the demon within and her spirit resisted. She fought like a wildcat, cursing them in a dizzying number of tongues, but as Dean completed the incantation, she uttered one final scream and came flooding out of her victim's mouth.

When the black smoke had cleared, dragged down into hell and vanished from the earth, an utterly final silence fell.

* * *

_Sam's head was spinning._

_He felt like his world had just received a huge jolt... one that he didn't even quite understand, to be honest. He gazed at Dean's grinning, somewhat embarrassed face in bafflement. He had a ton of questions, but Dean had already told him not to ask._

_Well... so that was how babies were made. Even though Dean had told him to avoid that at all costs._

_"Okaaay," Sam said slowly, because really, what else was he **supposed **to say? "Why are you telling me this again?"_

_"Future reference," Dean answered. "You're still a little young for this stuff, but you'll thank me later." He muttered something under his breath about Dad that Sam didn't quite catch, but just as quickly resumed his lecturing. "Right now, all you gotta worry about is getting girls to like you and going on nauseatingly cute little dates 'n stuff." Dean grinned conspiratorially. "So I'm gonna show you how it's done."_

* * *

Up close, Dean looked even worse. His appearance was almost haggard, utterly pale and strained, and the smile he attempted to give Sam was so half-assed that Sam's concern couldn't help but grow. "Saved your neck," Dean murmured triumphantly, but the effect was rather ruined by the heavy fluttering of his eyes.

"Yeah," Sam said, kneeling down next to the possession victim for a moment. She'd collapsed on the ground, unconscious, but her pulse was there, and she didn't appear to have any serious injuries.

"She okay?" Dean asked.

"She's alive." Sam rose and crossed the remaining space to Dean, crouching down beside his brother. "I'll call an ambulance soon. Where are you hurt?"

Dean's brows furrowed. "'m not going to the hospital," he said sullenly. "'m fine."

"Of course you are," Sam said patiently. "Now tell me where it hurts most."

Dean sighed, looking frustrated. "It _doesn't_, Sammy."

Sam indicated the dried blood coating Dean's neck and flecking his collar, and Dean waved it aside. "Just some scratches. Bitch was strong... didn't like it when I fought back."

"She did a bit more than that," Sam said in concern, inspecting the scabbed over scratches despite Dean's weak protests. "You can't even stand, Dean."

"Yeah, well... they drain you in your sleep. And they can make you sleep. She had something-"

"-on her lips, I know." Sam recalled the rest of the hasty research he'd done before he'd gone after the demon. Succubi typically operated by seducing men and draining their life force while they slept. The process took several days, and Sam was counting fervently on the fact that the succubus had only had Dean for a day... and that the process itself wasn't like half the lore suggested it was. With luck, she hadn't drained him enough to actually lessen his lifespan, though Dean looked so exhausted that Sam wanted to get him to a hospital regardless.

But Dean was adamant, and even in his weakened state, it was hard to argue with him. Sam relented after extracting a promise that they'd go to the hospital immediately if it got any worse, and truthfully, it was a bit of a relief not to go at the moment. This would be a hard one to explain.

After he'd carefully made sure that Katrina had none of Dean's DNA under her fingertips and wiped her hands as best he could, checking a bit more thoroughly for injuries as he did, Sam returned to find Dean struggling to stand. The older Winchester wasn't succeeding much, and Sam had to lunge to catch him when Dean's legs buckled, just as soon as he loosened his grip on the desk. Sam pretend not to noticed his brother's embarrassment, but this became a little more difficult when supporting Dean from one side also failed. Dean just couldn't keep to his feet.

"I'm gonna have to carry you," Sam finally said, reluctant because he knew exactly how Dean was going to react to that.

Dean's eyes flashed. "No way in _hell_," he wheezed.

"Dean, we need to get out of here."

"I'm not some damned helpless chick..."

"No one's calling you one."

"I can walk!"

"You _can't_," Sam growled, finally beginning to lose his patience and part of his temper, thanks to nerves frayed from worrying. "You can barely move, and you're lucky I don't dump your ass with a doctor right away."

The threat did its job. Dean subsided sulkily and did not continue arguing, though Sam suspected it also had something to do with the fact that the older Winchester's face was gray with exhaustion. He'd clearly used up all his energy just from talking and trying to move, though his silence was likely also related to his discomfiture at the situation.

Sam, for his part, could care less about Dean's wounded pride. All that mattered was the bodily wounds, which caused him far more concern than he let on, and so it was without a hint of embarrassment that he lifted his brother clear off the ground, like a child. Normally, such a feat would have left his arms aching after a few moments - Dean may have been smaller, but he didn't lack muscle - but something about his brother was emaciated and lighter, just as he'd feared. It was only with some difficulty that Sam made his way out of the darkened house, and Dean didn't speak another word. His eyes were sliding closed, his head tipping against Sam's shoulder, and by the time they'd reached the Impala, he was out.

After having gently placed Dean in the backseat, mindful of waking him, Sam slid into the driver's seat and pulled out his cell, dialing for emergency. As he gave the address, his eyes rested on the rear-view mirror, watching vigilantly over his sleeping brother.

* * *

_Dean had pointed out the girl - a beautiful brunette, a senior like him, sitting near the center of the courtyard and chatting with her friends. Sam watched as Dean approached nonchalantly, and despite himself the younger Winchester observed with rapt attention - partly out of curiosity and partly out of admiration for his older brother._

_He couldn't hear what was being said, because Dean had first emphasized the importance of body language and had instructed Sam to watch only. And watch Sam did - as Dean sauntered over, casually inserted himself into the conversation, and flashed the girl a winning smile._

_Her friends were giggling behind their hands, but the girl only gazed up at Dean coolly as he asked her something. She took her time responding, and when she did, it didn't take a genius to recognize the sarcasm in her head tilt and expression. Sam's hand flew up to his mouth to contain a snort as Dean made another comment, obviously trying to salvage the situation, but it was too late. With a huff, the girl stood and motioned for her friends to come, and she brushed past Dean without so much as a second glance at him. A few of her friends, still giggling, gave him sympathetic looks as they passed._

_Sam tried to compose his own amused expression as best he could before Dean returned._

* * *

Dean was sprawled out on one of the two beds in their motel room, and it was to Sam's great relief that he was snoring.

The younger Winchester had done everything he could to ensure Dean's health - cleaning and bandaging the scratches on his neck and making sure that no other injuries were hidden somewhere. But there were none, only that prevailing weakness and exhaustion that worried Sam deeply. Dean had hardly woken since he'd crashed at the victim's house, and Sam could only hope that sleep meant his body was recovering. After all, there was no better method of healing, right?

Sam was in the middle of poring over their father's journal for any mention of succubi that he might have missed when he heard Dean mutter something. "... -nt pie," the older Winchester snorted, and Sam glanced up to see Dean's eyes fluttering open, blinking rapidly. For a moment, he gazed at the ceiling in confusion, then sighed.

"There's pie over there," Sam said, jerking his head at the plastic bag that rested on his own bed, and Dean lifted his head, first peering blearily at Sam and then gazing in the indicated direction.

"You are awesome, Sammy," Dean said hoarsely, but a moment later, Sam snatched up the bag and tucked it farther away, despite Dean's cry of protest.

"You can have some once I'm sure you can hold stuff down," Sam said. "I also got some rice and crackers, so you can start with that."

Dean groaned as he slowly pushed himself up, and thankfully, it was a groan of annoyance, not pain. "You're such a mom," he said sullenly, clutching at his middle and trying not to make it obvious.

"And your stomach's completely empty," Sam retorted. "You eat pie, you're gonna hurl. You can have it later."

As he fished out the simpler foods and handed them to his brother, Dean scowled but did not complain. In fact, now that he was looking at food, he seemed reluctant to start eating. Sam didn't want to push him, either, and there was that pressing issue in the back of his mind that needed to be dealt with. It was better to get it out of the way now, he thought.

Sam took a seat at the edge of his bed, across from his brother. "Dean," he began and hated it. He didn't _want _to know, because the wrong kind of response meant he hadn't given the bitch a slow enough death. "Listen. I need to know what happened while she had you. If..."

Dean snorted and cut him off, grabbing a pack of crackers and tearing it open. "She didn't rape me, if that's what you're asking," he said, with so much frankness that Sam nearly slipped off the bed. "She didn't have time. And that first bit was consensual, I'll admit."

Sam made a face. "Ew."

"Yeah," Dean said darkly. "I think she just wanted the sex, though. There was nothing inhuman about it, let me tell you."

"God, Dean... please stop there."

It was relieving to see Dean grin... a mischievous little expression, and while it may not have run all the way through, even just a surface grin was enough at this point. "You sure?"

"I will throw that pie out the window."

Dean shut up, then; good food was an effective motivator. He took a hesitant bite of a cracker and appeared to have a little difficulty swallowing, so Sam reached back over the bed to grab one of the water bottles he'd also bought.

"Good ol' Sammy, thinkin' of everything," Dean said, gratefully accepting the water. Sam waited patiently while he ate a little more, and sure enough, the older Winchester continued abruptly. "They need you asleep to drain you, I guess. Not sure how they do it, but it doesn't involve sex. Just... creepy-ass dreaming."

Sam didn't bother to ask what that entailed. He nodded once. "How _did _you wake up?" he asked slowly, because the succubus definitely hadn't been expecting Dean to be awake when she'd brought Sam to her house.

Dean shrugged. "Just did. She probably underestimated me. Or somethin'. That dosage still packed one hell of a punch, though." He shook his head, then glanced at Sam, narrowing his eyes. "What about you? I thought all the lore says that men can't resist a succubus."

It was Sam's turn to shrug, uncomfortable. "Yeah, well... I wasn't looking for sex in the first place. And... there was something more important, I guess."

Dean's eyes softened a little. "I'm fine, Sam," he said, his voice uncommonly gentle.

Sam considered this and found that he believed it. Dean wasn't lying to him; he spoke far too candidly, and there was no avoidance or defensiveness in his movements and words. All that remained was to see how badly Dean's health was affected, though judging by the way he was now tearing into the crackers, it might not have been as bad as Sam feared.

He felt some of the apprehensive tightness in his chest begin to ease. It had been a while since he'd felt this much fear; but then again, it had been a while since Dean had ever been in any serious, prolonged danger.

"Jesus, you look like I just came back from the dead or somethin'. Or like someone just told you off." Dean chuckled. "Is that the only face you can pull?"

"Yes," Sam said shortly, and a few moments later, he couldn't help cracking a small grin in return.

* * *

_"That," said Dean, "is when you know she's too good for you."_

_Sam had to admit, Dean took defeat fairly gracefully. However, he looked a bit sullen as he returned to their bench, and Sam didn't say anything, though he was tempted to. For a moment, they sat in silence, as Dean struggled to absorb the blow to his pride, and then the younger Winchester voiced a question._

_"But... isn't the point of finding someone that they're always going to be too good for you?"_

_"A permanent someone, yeah," Dean said with a shrug. "We don't really have that luxury, life we lead."_

_That didn't sound very appealing to Sam. If he was going to date someone, then he'd want to stick with them. Why else would he hang around them in the first place?_

_"So that's why you settle for what you can get, or a chick who knows it's not serious," Dean said, and it sounded like he was once again warming to delivering a lesson. "So that you can..."_

_Sam had a feeling about where this was going. "No, thanks," he interrupted hastily, getting to his feet. He didn't want to hear anything more about bees, or whatever weird thing Dean had called it. "I don't really think that's for me, Dean."_

_He half-expected Dean to get annoyed with him, but his brother merely grinned and reached out a hand to ruffle Sam's hair. "You might be singing a different tune one day, kid," Dean laughed. "Then you'll be begging me to teach you."_

_"I don't think so," Sam said, returning the smile, and he ducked away from Dean's hand just as the bell rang, signaling the end of lunch. "See ya!"_

_Dean watched as his little brother ran off, mingling with the gathering crowd of students making their way back into the building. The older Winchester took his time in getting to his feet; honestly, he wasn't too concerned about getting to class on time. Instead, he trailed at the end of the crowd, keeping an eye on Sam until Sam could no longer be seen._

_Dean was still smiling faintly, though mostly in thought. "Weird kid," he said fondly and entered the school building._


End file.
